Hosted by Runpoint Partners’ founders Sam Gaddis (tech entrepreneur & AI builder) and Matthew Hall (PE operator & growth strategist), Runpoint Podcast strips the hype from artificial intelligence and shows you how to turn it into concrete business results—fast.

Runpoint: AI Business Transformation Podcast
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Hosted by Runpoint Partners’ founders Sam Gaddis (tech entrepreneur & AI builder) and Matthew Hall (PE operator & growth strategist), Runpoint Podcast strips the hype from artificial intelligence and shows you how to turn it into concrete business results—fast.
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Publishing Since
4/25/2025
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Recent Episodes

May 20, 2026
Runpoint 12: Agents Are Moving Into the Enterprise: Google, SAP, Salesforce, and the Future of Work
<p>AI agents are no longer just standalone demos. They are moving directly into the systems where work already happens: Google Workspace, SAP, Salesforce, email, calendars, files, CRMs, and enterprise systems of record.</p><p>In this episode of the Runpoint Podcast, Sam Gaddis, Matthew, Ryan Mish, and guest Harrison Wells of Dodo Digital discuss the shift from flashy AI tools to operational AI workflows. They cover Google Spark and Omni, the SAP + Anthropic partnership, Salesforce’s reported engineering productivity gains, Pi agents, Codex 5.5, Claude, and why many companies are increasing AI budgets faster than they are building true AI readiness.</p><p>The big question: will enterprises actually transform around AI, or will they just bolt chatbots onto old systems and call it innovation?</p><p>Timestamps<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I">00:00</a> — Intro: agents are moving into real work surfaces<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=138s">02:18</a> — Pi agents, Codex 5.5, and custom AI workflows<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=360s">06:00</a> — Google Spark, Omni, and the Workspace distribution advantage<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=746s">12:26</a> — Could Google own the enterprise AI surface?<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=919s">15:19</a> — Agents making purchases and real-world decisions<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=1263s">21:03</a> — SAP + Anthropic: Claude inside systems of record<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=1405s">23:25</a> — Why chatbot-style enterprise AI often fails<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=1530s">25:30</a> — Daily AI reports, heartbeat workflows, and what actually works<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=1904s">31:44</a> — Salesforce’s AI engineering productivity claims<br><a href="https://www.youtube.com/watch?v=CBtrRrbPO7I&t=2241s">37:21</a> — AI budgets are rising, but readiness is lagging<br>39:48 — How companies should build real AI adoption<br>42:31 — Why engineering is ahead of the rest of the enterprise<br>43:21 — Closing</p><p><br></p>

May 12, 2026
Runpoint: E11 - Anthropic Event, Designing with LLMs, the Proliferation of AI Consultants
<p>Runpoint Podcast E11: Code with Claude, the SaaSpocalypse, and AI Consulting Goes Mainstream<br>Back after a couple months off, with a bigger crew this time. Sam and Matthew are joined by Ryan Mish, one of Runpoint's operator engineers, and Thanh Pham of Signal Advisory.<br>Matthew just got back from Anthropic's Code with Claude conference and gives a side-by-side of the vibe at Anthropic vs. OpenAI (he hit both in the same week). From there we get into the stuff that's actually on our minds:</p><p>The flood of new "AI consulting firms" charging $20K to install Claude Code and call it a deployment, and what separates real work from theater<br>Whether the SaaSpocalypse is real, when it makes sense to rip out HubSpot, and where SaaS still wins (network effects, niche infrastructure, the school district that no VC will ever touch)<br>Why mid-market companies often only use 10% of the software they pay for, and what changes when the data finally talks to itself<br>Getting good design out of LLMs: Claude's house style vs. Codex 5.5 with image-gen mockups, and why Claude Design is still a prototyping tool<br>Closing round of what each of us is using right now: managed agents, Pi as a harness for steering Claude and Codex together, a PNPM supply chain attack PSA, HTML artifacts instead of Markdown, and a $30 conference swag computer turned into a reading game for Matthew's daughter</p><p>Chapters<br>00:00 Intro and new faces<br>01:30 Matthew's report from Code with Claude<br>05:30 Anthropic vs. OpenAI, in person<br>10:15 The AI consulting gold rush<br>14:30 Change management and company size<br>30:00 Is the SaaSpocalypse real?<br>40:30 Replacing software you only use 10% of<br>45:00 Getting good design out of LLMs<br>52:00 What we're using right now: managed agents, Pi, PNPM, HTML artifacts, and a tiny computer</p><p>Guests<br>Thanh Pham, Signal Advisory</p>

January 2, 2026
2025 AI Recap & 2026 Predictions: Winners, Losers, and What's Actually Working
<p>Happy New Year! In this episode, Matthew and Sam break down what actually happened in AI during 2025 and make predictions for what's coming in 2026.</p><p>We cover the biggest winners and losers, the apps and tools that changed how we work, who to follow for smart AI takes, what surprised us most, and where we think things are headed.</p><p>Key topics:<br>• Why companies that stayed curious won 2025<br>• OpenAI's fall from dominance to a three-horse race<br>• Claude Code and why it changed everything<br>• The tools we actually use daily (Whisper Flow, Granola, Cursor)<br>• Why vibe coded apps are passing enterprise code reviews<br>• Google's image generation breakthrough<br>• Our custom CRM build and the future of back office AI<br>• Why product managers are the winners of 2026<br>• The coming downfall of SaaS and low-skill trades</p><p>Plus: We launch our new Run Point Magazine and Sam accidentally emails hundreds of people.</p><p>🔗 Get the Run Point Magazine: [link]<br>🔗 Subscribe to our newsletter: [link]</p><p>---</p><p>## Chapters</p><p>0:00 - Intro & Happy New Year<br>0:39 - Biggest Winner of 2025: Curious Companies<br>2:16 - Claude Code Changed Everything<br>4:04 - Biggest Loser of 2025: AI Resisters<br>5:25 - Why OpenAI Lost Ground in 2025<br>7:07 - Best App of 2025: Claude Code & Whisper Flow<br>9:17 - Granola, Transcripts & the Transcript-to-Action Pattern<br>10:29 - Why Cursor Won the IDE Wars<br>11:33 - Best Thinkers to Follow: Tyler Cowen & Twitter Curation<br>14:40 - The Run Point Magazine Launch (and Email Disaster)<br>17:17 - Biggest Surprise: Enterprise-Grade Vibe Coded Apps<br>20:35 - Google's Image Generation Breakthrough<br>22:53 - Best Thing We Built: The AI-Powered CRM<br>27:08 - Worst Things We Built: Complex RAG Systems<br>28:52 - 2026 Predictions: Product Managers Win Big<br>30:37 - 2026 Loser Prediction: Half of SaaS Dies<br>32:28 - Why Low-Skill Home Services Are in Trouble<br>35:04 - AGI Is Basically Here (Contrarian Take)<br>38:10 - Why "Vibe Coding" Will Get Rebranded<br>38:38 - 2026 Resolutions: Back Office AI & Continuous Learning<br>41:01 - Wrap Up</p>
13 total episodes available
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